Wiltshire Vacation Rentals

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Our top choices for Wiltshire vacation rentals

Bev Rosevilla

Bev Rosevilla
2.5 star property
Rhyne Park Village
The price is CA $116
CA $176 total
includes taxes & fees
May 6 - May 7
Bev Rosevilla

Serenitys Hideaway Montego Bay

Serenitys Hideaway Montego Bay
3.5 star property
Montego Bay
The price is CA $83
CA $233 total
includes taxes & fees
May 19 - May 20
Serenitys Hideaway Montego Bay

Half Hill 3BR

Half Hill 3BR
3.5 star property
Montego Bay
The price is CA $469
CA $677 total
includes taxes & fees
May 10 - May 11
Half Hill 3BR

Short and longTerm ,Vacational rental home.

Short and longTerm ,Vacational rental home.
Rhyne Park Village
8.8 out of 10, Excellent, (3 reviews)
"Kadean is the best!.. very helpful everyday of my stay.."
United States
Julia M.
The price is CA $122
CA $149 total
includes taxes & fees
May 21 - May 22
Short and longTerm ,Vacational rental home.

Eden Luxe 1

Eden Luxe 1
2.5 star property
Montego Bay
10.0 out of 10, Exceptional, (2 reviews)
"The place was beautiful. Staff was friendly and helpful with the check in process. Will be planning another visit in the near future."
United States
Kelleia
The price is CA $313
CA $463 total
includes taxes & fees
May 7 - May 8
Eden Luxe 1

Sunshine Lodge- Your Home Away From Home

Sunshine Lodge- Your Home Away From Home
4.0 star property
Montego Bay
7.4 out of 10, Good, (3 reviews)
"It was beautiful on the inside and had an amazing view of Montego Bay."
United States
AGNES
The price is CA $94
CA $117 total
includes taxes & fees
Jun 5 - Jun 6
Sunshine Lodge- Your Home Away From Home

Rose Hall

Rose Hall
3.5 star property
Montego Bay
10.0 out of 10, Exceptional, (1 review)
"Great house and wonderful caretaker! Wish we had more time there!"
United States
Deborah
The price is CA $375
CA $637 total
includes taxes & fees
May 9 - May 10
Rose Hall

Nianna Luxurious Villa

Nianna Luxurious Villa
3.5 star property
Montego Bay
8.4 out of 10, Very good, (6 reviews)
"The property was beautiful and offered great views and even had a small private pool. The space was welcoming and large, perfect for a small family! We do recommend the resort, especially during hot months, to have the AC units serviced appropriately as there aren’t many close dining options so most meals are prepared in the home, and no AC in the kitchen was miserably hot. We did have a difficult time after check in to get in touch with the resort to arrange transportation in a timely manner....
United States
William
The price is CA $367
CA $525 total
includes taxes & fees
May 10 - May 11
Nianna Luxurious Villa

Hospitality Expert CB1: Pool, Beach & Chef

Hospitality Expert CB1: Pool, Beach & Chef
Montego Bay
8.8 out of 10, Excellent, (10 reviews)
"Had a good experience shower pressure, and bathroom flushing was a lil problem otherwise all was well for me"
United States
Kevin D.
The price is CA $198
CA $342 total
includes taxes & fees
May 21 - May 22
Hospitality Expert CB1: Pool, Beach & Chef

Montego Bay Ironshore Luxury Studios

Montego Bay Ironshore Luxury Studios
3.0 star property
Ironshore
9.4 out of 10, Exceptional, (26 reviews)
"Very close to the airport and safe."
United States
Chukwufumnaya
The price is CA $92
CA $108 total
includes taxes & fees
May 17 - May 18
Montego Bay Ironshore Luxury Studios

Hummingbird Room in Guest Home: WiFi, Hot Water AC Montego Bay Live-in Hosts

Hummingbird Room in Guest Home: WiFi, Hot Water AC Montego Bay Live-in Hosts
Mount Salem
10.0 out of 10, Exceptional, (1 review)
"I stayed at Topaz Dream Guesthouse in Montego Bay during Sumfest 2025, and it was such a beautiful and unforgettable experience. The space is cozy, artistic, and full of character, but what truly makes it special is Cherri, the host.Cherri is warm, wise, and simply amazing. She carries the spirit of Jamaica in her heart and has the most incredible stories of life, love, triumph, and resilience. Connecting with her was the true highlight of my trip—our conversations left me feeling inspired and...
United States
English C.
The price is CA $68
CA $109 total
includes taxes & fees
May 22 - May 23
Hummingbird Room in Guest Home: WiFi, Hot Water AC Montego Bay Live-in Hosts

Villa Nilaja

Villa Nilaja
5.0 star property
Ironshore
10.0 out of 10, Exceptional, (1 review)
"I booked a destination for my 21 year old daughter birthday and she had aworry free amazing time. The host setup everything my daughter wanted to do flawlessly! The private chef was exceptional with Jamaican and American cuisine! The driver was always out front and on time! Can't wait for the next visit!"
United States
Nakish
The price is CA $1,301
CA $1,701 total
includes taxes & fees
May 22 - May 23
Villa Nilaja

Impeccable Spacious 3 Bedroom Home Near Beach!

Impeccable Spacious 3 Bedroom Home Near Beach!
Montego Bay
9.0 out of 10, Wonderful, (7 reviews)
"Our stay at this property was pleasant, relaxing and quiet. Host was very responsive and checked in during our stay to make sure all was well. There is a local grocery store and restaurant within walking distance which was a plus. Will definitely stay again!"
United States
Bridgette E.
The price is CA $122
CA $218 total
includes taxes & fees
May 7 - May 8
Impeccable Spacious 3 Bedroom Home Near Beach!

Angels Hideaway Blue Room

Angels Hideaway Blue Room
2.0 star property
Ironshore
9.0 out of 10, Wonderful, (2 reviews)
"Very convenient location, very affordable. And very clean. The host took good care of us. "
United States
DUSTIN
The price is CA $105
CA $123 total
includes taxes & fees
May 7 - May 8
Angels Hideaway Blue Room

Claudeville Condo

Claudeville Condo
3.0 star property
Montego Bay
8.6 out of 10, Excellent, (24 reviews)
"Staff was very friendly and welcoming. "
United Kingdom
Sophia
The price is CA $130
CA $151 total
includes taxes & fees
May 17 - May 18
Claudeville Condo

Unity Villa

Unity Villa
3.0 star property
Montego Bay
8.0 out of 10, Very good, (1 review)
"I LIKE HOW THEY COMMUNICATED AND ADDRESSED THE PROBLEMS ! Only thing I didn’t like was the no working ac and there wasn’t stuff close to go shop "
United States
Susan
The price is CA $128
CA $176 total
includes taxes & fees
May 10 - May 11
Unity Villa

Nianna Chatham

Nianna Chatham
2.5 star property
Hip Strip
The price is CA $186
CA $297 total
includes taxes & fees
May 6 - May 7
Nianna Chatham

Hospitality Expert SWF104 - Pool, Beach, Chef

Hospitality Expert SWF104 - Pool, Beach, Chef
Montego Bay
10.0 out of 10, Exceptional, (2 reviews)
"Nice place and breakfast"
Spain
Xavier
The price is CA $184
CA $324 total
includes taxes & fees
May 21 - May 22
Hospitality Expert SWF104 - Pool, Beach, Chef

Firefly cottage with Ocean view

Firefly cottage with Ocean view
Cave District
10.0 out of 10, Exceptional, (27 reviews)
"I would recommend this cabin resort to anyone. Geneva was wonderful host, along with her beautiful family"
United States
Rick B.
The price is CA $94
CA $121 total
includes taxes & fees
Jun 1 - Jun 2
Firefly cottage with Ocean view

The Best 2 Bedrooms Townhouse in Montego Bay!

The Best 2 Bedrooms Townhouse in Montego Bay!
Ironshore
8.6 out of 10, Excellent, (7 reviews)
"Chester was the best host EVER!!!"
United States
Weslyn A.
The price is CA $340
CA $389 total
includes taxes & fees
May 22 - May 23
The Best 2 Bedrooms Townhouse in Montego Bay!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Wiltshire Hotel Reviews

Find out more about Wiltshire

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Wiltshire. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find vacation rentals in Wiltshire?

Yes, we have vacation rentals close to well known points of interest in Wiltshire, or you can select a more remote option if you're looking for relaxation. Wiltshire is known for its beaches and sporting events. Make sure you have time to check out the shopping and restaurants during your trip.

What are some of the best vacation rentals in Wiltshire?

Bev Rosevilla: You might want to consider this vacation home rental near Wiltshire, which offers a terrace, a private yard, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave, and kitchenware. You and your friends and family can relax into your vacation with amenities like a selection of games.

What’s there to see and do in Wiltshire?

While exploring the area, visit family-friendly sights like Montego Bay Marine Park, or get outside and enjoy nature at Freeport Peninsula. In the larger area, you’ll find Montego Bay Cruise Ship Terminal and Saint James Parish Church.

What’s a vacation rental in Wiltshire like?

Vacation rentals are privately owned properties you can book for a couple of days or more in Wiltshire. Vacation rentals provide amenities like laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a clean environment, a vacation rental can offer a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for a small group gathering.